


Prestidigitation

by keefling



Series: Playdates [1]
Category: Critical Role (Web Series)
Genre: Boot Worship, Casual Sex, Frottage, Light Dom/sub, M/M, Masturbation, Oral Fixation, Praise Kink, Trans Male Character
Language: English
Status: Completed
Published: 2018-06-14
Updated: 2018-06-14
Packaged: 2019-05-23 04:17:14
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,515
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14926989
Author URL: https://archiveofourown.org/users/keefling/pseuds/keefling
Summary: Molly and Caleb have a playdate with a pair of thigh-high leather boots.





	Prestidigitation

**Author's Note:**

> Written for a [criticalkink fill](https://criticalkink.dreamwidth.org/3194.html?thread=597882#cmt597882) requesting boot worship. 
> 
> This is my first fic as @keefling! I have been posting under the name sundance, but I wanted my username to match my twitter & tumblr. 
> 
> Note: Caleb is a trans man in this fic, and I use feminine-coded words to describe his genitals.

The party had taken their usual table at the inn after a day spent trudging through the swamp.  They had tracked mud all the way inside and together they did not smell great—terrible, actually, even to Caleb who was used to the musty scent of dirt and grime.  Their clothes were soaked up to their knees and their boots were caked in muck and stunk of decay. 

All except for Mollymauk, whose outfit was impeccably clean.  The tiefling had seemed to materialize beside Caleb, sitting cross-legged in a pristine pair of trousers and boots that looked like they could have been brand new.  Caleb wondered how he did it; soap and water could only clean so much dirt off of their ruined clothes, and the party had little to spare.  Perhaps it was the mystery that drew him in.  Once a question formed in Caleb’s mind, he was never sated until he found an answer.  He kept glancing down at Molly’s legs, watching the pointed toe of his boot bounce idly underneath the table. 

Caleb’s interest crept towards the line of obsession the longer they stayed in the swamplands.  He would hang his own clothes up to dry at night and shimmy into his damp trousers the next morning, yank on his soggy boots and throw his ever-filthy coat over his shoulders.  Then Molly would show up in his spotless coat and thigh-high leather boots, looking like he had never stepped foot outdoors in his life. 

Caleb could have just asked, but the opportunity never came up until one evening when Molly stopped him in the hall with a curious look on his face. 

“Caleb,” Molly said, stepping in front of the wizard and blocking the hallway.  Caleb’s skin prickled in nervous anticipation. “You’ve been paying quite a lot of attention to my boots lately.  Tell me I don’t have something stuck to my heel?” Molly twisted to look behind him, pretending to examine the bottom of his heel. 

“No,” Caleb answered.  He cursed himself for leaving his coat in his room; he desperately wanted to hide under something.  “I have just been wondering how you keep them so clean.  We are up to our knees in shit every day.  You must have some kind of trick, _ ja? _ ” 

Molly shrugged.  “Oh, you didn’t know?  Prestidigitation works wonders on just about anything.”

“Oh, I….that….that would explain it.”  It was so obvious that Caleb wanted to slap himself for overseeing it. 

“Hmm, indeed, but it doesn’t quite explain why you’ve been staring so hard at my shoes, if all you were concerned with was tidiness,” Molly said.  He had his hands clasped loosely behind his back while leaning forward, sizing up Caleb.  “Especially since you’re normally so fixated on my ass.” 

Caleb coughed hard into his sleeve.  “I am not—I haven’t been—”

“Oh, Caleb, spare me,” Molly groaned.  “There’s nothing to be ashamed of, darling.  It’s a good ass.” 

“And those are good boots,” Caleb replied.  His heart beat rapidly in his chest.  He tried to look anywhere but Molly’s feet, but it was difficult when making eye contact was even worse. 

Molly tipped Caleb’s head up with a finger under his chin, bringing their faces closer together.  There was something hopeful in the way he was smiling. 

“I wouldn’t mind showing you just how good these boots can be,” Molly said, his voice dropping to a pitch that resonated in Caleb’s lower abdomen. 

“How so?” Caleb asked, wincing as his voice cracked.  He could barely breathe. 

Molly grinned wide.  He leaned into Caleb’s space, caressing Caleb’s cheek with his fingertips.  “Come find out for yourself.  Do you want to play, Caleb?”

“Yes,” Caleb whispered against Molly’s lips.  The question held so much weight and mystery, but Caleb felt starved for whatever Molly was offering. 

“Wonderful!” Molly said, cheerfully, stepping back.  “Follow me.” He suddenly turned around, looked over his shoulder and gave Caleb an exaggerated wink.  He whacked Caleb’s thighs with his tail before striding away down the hall, heels tapping on the wooden floorboards. 

Caleb felt weak in the knees as he stumbled after the tiefling.  When he reached Molly’s room, he found Molly sitting in a wooden chair by the tiny desk in the corner.  Molly sat with his legs spread and his feet planted firmly on the floor.  It was a completely reasonable way to sit, Caleb tried to convince himself, but then he imagined himself wedged between Molly’s knees and all logic melted away. 

“Take those filthy trousers off,” Molly said, waving a hand at Caleb.  “You smell like shit.”

Caleb laughed weakly and did as he was told.  Molly’s voice had an unusually authoritative quality to it, which seemed to bypass any reluctance Caleb had to comply.  He folded his damp trousers and set them and his boots out of the way.  He might as well have been naked, standing there in his linen shirt and underclothes while Molly remained fully dressed. 

“That’s much better,” Molly purred.  “Now, come here.” He beckoned Caleb with two crooks of a finger and, as if attached to an invisible chain, Caleb dropped to his knees before Molly.  Molly cupped Caleb’s cheek and swiped his thumb over his parted lips. 

“Before we begin, I need to know what your boundaries are,” Molly said, his voice firm but gentle in contrast to the commanding tone from a moment ago. 

“Do not hit me, or degrade me,” Caleb said.  “Hair pulling is….is fine.” 

“Ooh, I can work with that,” Molly beamed.  “Is there anything else?” 

“I-I cannot think of anything right now,” Caleb murmured, turning his face in towards Molly’s palm.  He was losing the battle with the lusty haze that surrounded the thinking parts of his brain.

“Now, Caleb, this is very important.”  Molly turned Caleb’s head to look at him again.  “If you are uncomfortable with anything we do, you will tell me, and I will stop immediately.”

“Yes, Mollymauk, I will.”  Caleb fidgeted with his hands.  He was getting impatient, eager to please Molly. 

“Good boy,” Molly said, the sultry tone returning to his voice as he slid his thumb between Caleb’s teeth.  Caleb instinctively closed his lips around it. He swallowed up to the second knuckle, swirling his tongue around one of Molly’s rings and enjoying the contrast of cool metal inside his warm mouth.  Molly added his forefinger and playfully pinched Caleb’.  Caleb took both fingers inside, coating them in spit that also dripped down his chin.  Molly hummed appreciatively and withdrew his hand to lick the saliva from his fingers.

“As I was saying,” Molly said, as if they had been in the middle of a real conversation, “Prestidigitation can only do so much for these old boots.  Why don’t you put that lovely tongue of yours to work and finish the job?”

Caleb failed to suppress a full body shudder.  He took Molly’s foot in his hands, cupping the ankle in one and running his fingers over the seams with the other, all the way up to where the boot ended above Molly’s knee.  The brown leather was soft, smooth, and undoubtedly expensive.  The boots themselves were spotless, Caleb found as he brought Molly’s foot closer to inspect it, no dust or stains or worn-out parts.  

Caleb bowed his head and pressed his lips to the toe of the boot.  He gathered spit on his tongue and swiped it over the arch of Molly’s foot, savoring the feeling of the soft yet gritty material against his tongue. 

Molly was breathing heavily above him.  Caleb’s neck prickled pleasantly as he listened for the first signs of Molly’s coming apart.  He moaned performatively as he continued to lick Molly’s boot with wide sweeps of his tongue and was rewarded with a shaky sigh.  When he looked up he saw Molly’s pale-knuckled fingers gripped tightly around the left arm of the chair. 

“How am I doing?” Caleb asked.  The leather had turned a darker shade of brown from the moisture that had seeped into the fabric, showing where his tongue had been. 

“You’re doing a wonderful job, love,” Molly purred.  He had his head propped up by the hand not clenched around the arm of the chair and was gazing dreamily down at Caleb.  He let his foot fall from Caleb’s loose grip and raised the other, nudging Caleb’s chin with his toe.  “But you’re only halfway done.” 

“Of course, Mollymauk,” Caleb murmured, desire flaring in the pit of his stomach.  He was certain that he was wet by now; he shifted in his trousers and felt something sticky between his legs.  He set his own needs aside and began affectionately nuzzling Molly’s ankle. He kissed a line from ankle to toe and back again; he could feel the warmth of Molly’s skin through the thin material.  Caleb closed his eyes, letting his lips guide him over every arch and dip in Molly’s foot.  He bathed the boot with his tongue with the same attention and care as the other.  When he was done, he let his head fall into Molly’s lap, eyes closed and cheeks flushed. 

“Oh, Caleb,” Molly breathed, running his fingers through Caleb’s hair, “you’re such a good boy.  You spoil me, darling.  You make me feel like a god.” 

Caleb  _ whined. _  He lower back was sore from hunching over and his groin was aching and dripping with want. 

“Mmm, what was that?” Molly asked.  He wedged his toe between Caleb’s legs and lifted up, causing Caleb to gasp and shudder.  Caleb’s hips seemed to roll forward on their own, instinctively seeking contact.  A wicked grin split Molly’s face in two.  “Enjoying yourself down there?” 

“ _ Ja, _ Mollymauk,” Caleb managed, but his words turned to whimpers when Molly flexed his toes against Caleb’s clit.  Caleb dropped his weight and felt the toe press hard against his sensitive cunt.  He raised his ass and rocked his hips forward, grinding his clit into the arch of Molly’s foot.  He felt Molly’s hand tighten in his hair and he grunted encouragingly, although the guttural sound that escaped his lips could have meant anything. 

While Caleb steadily rutted against Molly’s foot, his face was inches away from Molly’s half-hard cock when Molly undid his trousers and pulled it out.  Molly began jerking himself to full hardness, arching his back as he did so.  Caleb stared, enchanted by the rings that adorned Molly’s fingers and glimmered in the light as he twisted his hand around his cock. 

Caleb’s fingers dug into Molly’s thighs just above the top of his boots.  He held on for dear life while he humped Molly’s foot like a horny dog.  He was not sure if he would be able to look Molly in the eye the next day, but he was in too far to stop.  Molly looked fucking good in those boots, and Caleb was happy to find that he felt just as good fucking them. 

Caleb had nearly rubbed himself raw by the time his orgasm crested, but when he came it was fantastic.  He closed his eyes, clenched his teeth and buried his face into the meat of Molly’s inner thigh.  His whole body trembled as the tension built and shook when it released.  He trapped Molly’s leg between his thighs as he clenched them together and came again with his clit pressed hard against Molly’s toe, his cum gushing through his underclothes and onto the leather with every contraction of his inner walls. 

Caleb heaved into the fabric of Molly’s trousers and clung to him until his orgasm subsided.  When he opened his eyes he saw Molly erratically fisting his cock, swollen and slick with precum.  Molly stared down at him with glossy eyes and his mouth hanging open.  He looked absolutely wrecked, and Caleb smirked with a sense of pride that he would be the one to crack the man who was always so collected and poised. 

“Mollymauk,” Caleb said to get his attention.  He licked his lips and extended his tongue. 

“Are you sure?” Molly asked, gripping his cock tight.  Caleb tilted his head back and nodded eagerly.  A few more strokes was all it took to shatter Mollymauk to pieces. 

“Fuck, you’re incredible,” Molly rasped.  “I’m about to cum, Caleb, get ready for it— _ ahh! _  I’m cumming, fuck, Caleb, cumming!”

Molly threw his head back and with a wail and came in Caleb’s mouth as promised.  Caleb tried to catch it the best he could.  Most landed on his tongue but some splashed on his cheek and dripped down his chin.  

“Sorry about that,” Molly mumbled once he floated back down to earth.  He swiped his thumb across Caleb’s cheek and licked his finger clean. 

“All good,” Caleb muttered, who was resting his head on Molly’s knee.  Molly’s cock, now spent, flopped to the side for Caleb to admire.  Meanwhile, Molly extricated his leg from between Caleb’s.  He caught the sight of the dark brown leather, soaked with Caleb’s cum. 

“Look at the mess you’ve made,” teased Molly, lifting his foot.  Caleb was horrified to see just how much he had drenched the leather. 

“Should I clean it again for you?” offered Caleb, although he made no effort to move from his current position. 

“Not today,” Molly decided, giving Caleb’s head a pat.  “You’ve been so kind to me, Caleb, such a good boy.  But now that I know helpful you are, I might have to ask you to clean my boots more often.” 

“I cannot say I am opposed,” Caleb admitted.  Once he regained his strength he stood with the help of Molly’s knees for leverage.  “I will see you on another night, Mollymauk, but it is very late.  I should be going now.”

Molly looked amused.  “Yes, for now you should worry about cleaning yourself up, darling.”  Caleb jerked away when Molly’s finger grazed his oversensitive clit through his soaked underclothes.  He hurried to yank his trousers on to hide the wet spot, but the fabric was still damp and felt unpleasant against his skin. 

Caleb thought about bolting for the door, but instead returned to Molly, who had just finished tucking his cock back into his trousers.  Caleb took Molly’s hand. 

“Thank you, Molly,” he said. 

“No need,” Molly said, crossing his legs and leaning to one side of the chair, “You are an excellent playmate.” 

Caleb shook his head.  “No, I mean it, thank you.  I needed that tonight, very much.” 

“I mean it, too, love.  Just come find me and I will give you anything that you need.” 

Caleb blushed and could not help but smile.  He gave Molly’s hand a squeeze before letting go.  “Have a good night, Mollymauk,” he said, heading for the exit. 

“Sweet dreams,” Molly called, waving while he watched Caleb close the door. 

Caleb snuck back into his room, got undressed in the dark and collapsed into bed.  Maybe he would not be able to look Mollymauk in the eye ever again, but after that night he knew that he would never let those boots out of his sight. 


End file.
